# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2010

data_global

_journal_coden_Cambridge         182
loop_
_publ_author_name
_publ_author_address
'Heron, Bernard'
;School of Chemistry
University of Leeds
Leeds, LS2 9JT, UK
;
'Gabbutt, Christopher'
;School of Chemistry
University of Leeds
Leeds, LS2 9JT, UK
;
'Kilner, Colin' ''
'Kolla, Suresh' ''

_publ_contact_author_name        'Heron, Bernard'
_publ_contact_author_email       b.m.heron@leeds.ac.uk

_publ_section_title              
;
Benzopentalenonaphthalenones from the intramolecular
capture of a merocyanine derived from a naphthopyran
;
_publ_contact_author_address     
;
School of Chemistry
University of Leeds
Leeds
LS2 9JT
UK
;
_publ_contact_author_phone       '+44 (0)113 34 32925'
#TrackingRef 'BMH1910.CIF'

_publ_requested_journal          
;
Chemical Communications
;

# Attachment 'BMH1910.CIF'

data_bmh1910
_database_code_depnum_ccdc_archive 'CCDC 787182'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C43 H34 O6'
_chemical_formula_sum            'C43 H34 O6'
_chemical_formula_weight         646.70

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c
_symmetry_space_group_name_Hall  '-C 2yc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   23.5830(17)
_cell_length_b                   16.0599(13)
_cell_length_c                   17.8227(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.983(3)
_cell_angle_gamma                90.00
_cell_volume                     6700.1(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8061
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      26.17
_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2720
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   none
_exptl_special_details           
;
The crystal temperature was held constant
using an Oxford Cryosystems
Cryostream 600 system.
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         
;
Bruker Nonius FR591 rotating anode generator
;
_diffrn_radiation_monochromator  
;
graphite model mounted in "parallel" mode
;
_diffrn_measurement_device_type  
;
Mach3 kappa-type 4-circle goniostat.
;
_diffrn_radiation_detector       'ApexII camera'
_diffrn_measurement_method       'rotation images'
_diffrn_detector_area_resol_mean 
;
120 microns
;
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            51816
_diffrn_reflns_av_R_equivalents  0.0785
_diffrn_reflns_av_sigmaI/netI    0.0531
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.98
_diffrn_reflns_theta_max         27.45
_reflns_number_total             7460
_reflns_number_gt                3901
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
APEX 2 software, Bruker Nonius 2004
;
_computing_cell_refinement       
;
APEX 2 software, Bruker Nonius 2004
;
_computing_data_reduction        
;
SAINT - Bruker Integration program embedded in
APEX 2 software, Bruker Nonius 2004
;
_computing_structure_solution    
;
SHELXS-97 (Sheldrick, G. M. Acta Cryst. (2008). A64, 112)
XSeed (L.J.Barbour, J.Supramol. Chem., 2003, 1, 189.)
;
_computing_structure_refinement  
;
SHELXL-97 (Sheldrick, G. M. Acta Cryst. (2008). A64, 112)
XSeed (L.J.Barbour, J.Supramol. Chem., 2003, 1, 189.)
;
_computing_molecular_graphics    'ORTEP-III Version 1.08 (Farrugia, 2005)'
_computing_publication_material  
;
enCIFer: A program for viewing, editing and visualising CIFs.
F. H. Allen, O. Johnson, G. P. Shields, B. R. Smith, M. Towler,
J. Applied Cryst., 37, 331-334, 2004
;

_refine_special_details          
;
Crystals appeared opaque but were actually very dark red when viewed
through thinner sections. Initial images from the diffractometer showed
a dramatic reduction of reflection intensity for angles greater than
18.5 degrees. However, using a combination of the largest good quality
crystal, high X-ray generator power, long collection times and high
redundancy, enabled a structure to be obtained.

The structure solved in the monoclinic spacegroup C2/c with one
molecule in the asymmetric unit.

All hydrogen atoms could be located in the Fourier difference map but, in
the final stages of the refinement, they were placed in calculated
positions and refined using a riding model. C-H distances: CH3, 0.98\A;
aromatic, 0.95\A.

All Uiso(H) values were constrained to be 1.2 times (1.5 for methyl) Ueq
of the parent atom.

The CIFcheck routine highlights a short intermolecular H...H contact
involving methyl hydrogen atoms. Specifically the interaction is between
neighbouring H51C...H51C and the distance is 2.09 angstroms (obtained
using the program Mercury*).
In some cases this may be due to the fact that the positions of the
H-atoms are not at the optimal calculated positions. A check was performed
by refining all the parameters of the C51 H-atoms from the X-ray data and
the H51C...H51C distance there was 2.08 angstroms indicating that the
calculated positions and those of the freely refined methyl H-atoms are
the same and so the calculated orientations of the C51 H-atoms are very
probably correct.

The five ring structures, C1 to C20, in neighbouring molecules lie in
parallel planes resulting in the close proximity of the C51 methyl groups.
The distance between these planes is 3.58 angstroms. This was measured,
using Mercury, by generating the plane through the C4 to C9 ring of one
molecule and then measuring the distance of that plane to the centroid
of the C4 to C9 ring in the neighbouring molecule.

* Mercury: visualization and analysis of crystal structures
C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields,
R. Taylor, M. Towler and J. van de Streek,
J. Appl. Cryst., 39, 453-457, 2006

C.Kilner 1 February 2010

Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0556P)^2^+12.0321P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7460
_refine_ls_number_parameters     447
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1310
_refine_ls_R_factor_gt           0.0611
_refine_ls_wR_factor_ref         0.1930
_refine_ls_wR_factor_gt          0.1379
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.06706(12) 0.77579(17) -0.05963(15) 0.0492(7) Uani 1 1 d . . .
C2 C 0.03427(12) 0.85492(17) -0.09317(15) 0.0500(7) Uani 1 1 d . . .
C3 C -0.01195(13) 0.85923(18) -0.14580(16) 0.0536(7) Uani 1 1 d . . .
H3 H -0.0286 0.8096 -0.1676 0.064 Uiso 1 1 calc R . .
C4 C -0.03648(13) 0.94030(19) -0.16936(16) 0.0530(7) Uani 1 1 d . . .
C5 C -0.08590(14) 0.9474(2) -0.22128(17) 0.0622(8) Uani 1 1 d . . .
H5 H -0.1041 0.8982 -0.2418 0.075 Uiso 1 1 calc R . .
C6 C -0.10880(15) 1.0240(2) -0.24342(17) 0.0677(9) Uani 1 1 d . . .
H6 H -0.1425 1.0271 -0.2785 0.081 Uiso 1 1 calc R . .
O7 O -0.10798(11) 1.17061(16) -0.24065(13) 0.0763(7) Uani 1 1 d . . .
C7 C -0.08250(15) 1.0969(2) -0.21429(17) 0.0632(9) Uani 1 1 d . . .
C8 C -0.03429(14) 1.0928(2) -0.16272(17) 0.0577(8) Uani 1 1 d . . .
H8 H -0.0166 1.1425 -0.1427 0.069 Uiso 1 1 calc R . .
C9 C -0.01132(13) 1.01494(18) -0.13971(15) 0.0517(7) Uani 1 1 d . . .
O10 O 0.06563(10) 1.07696(13) -0.05921(13) 0.0691(6) Uani 1 1 d . . .
C10 C 0.04036(14) 1.01310(19) -0.08383(16) 0.0542(7) Uani 1 1 d . . .
C11 C 0.06129(13) 0.92946(17) -0.05976(15) 0.0497(7) Uani 1 1 d . . .
C12 C 0.10624(12) 0.90826(16) -0.00743(15) 0.0483(7) Uani 1 1 d . . .
C13 C 0.14971(12) 0.94600(17) 0.04720(15) 0.0469(7) Uani 1 1 d . . .
C14 C 0.16287(13) 1.02891(17) 0.06448(15) 0.0500(7) Uani 1 1 d . . .
H14 H 0.1403 1.0730 0.0413 0.060 Uiso 1 1 calc R . .
O15 O 0.22906(10) 1.12434(12) 0.13738(11) 0.0638(6) Uani 1 1 d . . .
C15 C 0.21055(14) 1.04475(17) 0.11730(16) 0.0527(7) Uani 1 1 d . . .
C16 C 0.24246(13) 0.97979(18) 0.15282(15) 0.0525(7) Uani 1 1 d . . .
H16 H 0.2742 0.9919 0.1894 0.063 Uiso 1 1 calc R . .
C17 C 0.22831(12) 0.89695(17) 0.13518(15) 0.0481(7) Uani 1 1 d . . .
H17 H 0.2503 0.8530 0.1596 0.058 Uiso 1 1 calc R . .
C18 C 0.18202(12) 0.87932(16) 0.08192(14) 0.0458(7) Uani 1 1 d . . .
C19 C 0.15919(12) 0.79883(16) 0.04837(14) 0.0454(6) Uani 1 1 d . . .
C20 C 0.11406(12) 0.81820(16) -0.00429(15) 0.0477(7) Uani 1 1 d . . .
C21 C 0.18511(12) 0.71766(16) 0.07223(15) 0.0466(7) Uani 1 1 d . . .
C22 C 0.19964(13) 0.69954(17) 0.14943(15) 0.0527(7) Uani 1 1 d . . .
H22 H 0.1932 0.7405 0.1859 0.063 Uiso 1 1 calc R . .
C23 C 0.22292(14) 0.62427(17) 0.17364(16) 0.0551(8) Uani 1 1 d . . .
H23 H 0.2316 0.6136 0.2262 0.066 Uiso 1 1 calc R . .
C24 C 0.23373(13) 0.56381(17) 0.12153(16) 0.0522(7) Uani 1 1 d . . .
O25 O 0.25604(10) 0.49055(12) 0.15218(11) 0.0619(6) Uani 1 1 d . . .
C25 C 0.22115(13) 0.58012(17) 0.04438(16) 0.0505(7) Uani 1 1 d . . .
H25 H 0.2289 0.5395 0.0083 0.061 Uiso 1 1 calc R . .
C26 C 0.19725(13) 0.65631(17) 0.02076(16) 0.0503(7) Uani 1 1 d . . .
H26 H 0.1889 0.6670 -0.0318 0.060 Uiso 1 1 calc R . .
C31 C 0.09033(12) 0.73199(16) -0.12630(15) 0.0472(7) Uani 1 1 d . . .
C32 C 0.13771(13) 0.76368(17) -0.15621(15) 0.0501(7) Uani 1 1 d . . .
H32 H 0.1583 0.8086 -0.1313 0.060 Uiso 1 1 calc R . .
C33 C 0.15555(13) 0.73117(17) -0.22157(16) 0.0516(7) Uani 1 1 d . . .
H33 H 0.1878 0.7542 -0.2412 0.062 Uiso 1 1 calc R . .
O34 O 0.14724(10) 0.63676(13) -0.32291(12) 0.0650(6) Uani 1 1 d . . .
C34 C 0.12617(13) 0.66476(18) -0.25830(16) 0.0537(7) Uani 1 1 d . . .
C35 C 0.07967(14) 0.6317(2) -0.22939(18) 0.0632(8) Uani 1 1 d . . .
H35 H 0.0598 0.5858 -0.2537 0.076 Uiso 1 1 calc R . .
C36 C 0.06163(14) 0.66575(19) -0.16406(18) 0.0615(8) Uani 1 1 d . . .
H36 H 0.0290 0.6431 -0.1451 0.074 Uiso 1 1 calc R . .
C41 C 0.02969(13) 0.71999(18) -0.01552(16) 0.0525(7) Uani 1 1 d . . .
C42 C 0.04887(14) 0.64055(19) 0.00848(18) 0.0627(8) Uani 1 1 d . . .
H42 H 0.0844 0.6210 -0.0045 0.075 Uiso 1 1 calc R . .
C43 C 0.01723(16) 0.5900(2) 0.0506(2) 0.0732(10) Uani 1 1 d . . .
H43 H 0.0312 0.5365 0.0659 0.088 Uiso 1 1 calc R . .
O44 O -0.06304(13) 0.56002(19) 0.11059(18) 0.1039(9) Uani 1 1 d . . .
C44 C -0.03455(17) 0.6169(2) 0.0704(2) 0.0746(10) Uani 1 1 d . . .
C45 C -0.05405(16) 0.6956(2) 0.04888(19) 0.0727(10) Uani 1 1 d . . .
H45 H -0.0893 0.7152 0.0627 0.087 Uiso 1 1 calc R . .
C46 C -0.02137(15) 0.7462(2) 0.00650(18) 0.0627(8) Uani 1 1 d . . .
H46 H -0.0349 0.8004 -0.0075 0.075 Uiso 1 1 calc R . .
C51 C -0.07861(18) 1.2462(3) -0.2156(3) 0.0967(14) Uani 1 1 d . . .
H51A H -0.0759 1.2500 -0.1604 0.145 Uiso 1 1 calc R . .
H51B H -0.0998 1.2942 -0.2383 0.145 Uiso 1 1 calc R . .
H51C H -0.0401 1.2457 -0.2310 0.145 Uiso 1 1 calc R . .
C52 C 0.19846(17) 1.19204(19) 0.09912(19) 0.0749(10) Uani 1 1 d . . .
H52A H 0.2005 1.1876 0.0447 0.112 Uiso 1 1 calc R . .
H52B H 0.2155 1.2449 0.1179 0.112 Uiso 1 1 calc R . .
H52C H 0.1584 1.1900 0.1086 0.112 Uiso 1 1 calc R . .
C53 C 0.27045(17) 0.42704(19) 0.10228(19) 0.0701(9) Uani 1 1 d . . .
H53A H 0.2365 0.4116 0.0679 0.105 Uiso 1 1 calc R . .
H53B H 0.2847 0.3782 0.1316 0.105 Uiso 1 1 calc R . .
H53C H 0.3001 0.4476 0.0729 0.105 Uiso 1 1 calc R . .
C54 C 0.11503(16) 0.5732(2) -0.36482(19) 0.0719(10) Uani 1 1 d . . .
H54A H 0.1144 0.5231 -0.3335 0.108 Uiso 1 1 calc R . .
H54B H 0.1327 0.5601 -0.4104 0.108 Uiso 1 1 calc R . .
H54C H 0.0759 0.5927 -0.3793 0.108 Uiso 1 1 calc R . .
C55 C -0.1208(2) 0.5753(3) 0.1172(3) 0.1096(15) Uani 1 1 d . . .
H55A H -0.1239 0.6241 0.1496 0.164 Uiso 1 1 calc R . .
H55B H -0.1373 0.5267 0.1397 0.164 Uiso 1 1 calc R . .
H55C H -0.1414 0.5860 0.0670 0.164 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0539(18) 0.0449(15) 0.0479(15) -0.0062(12) 0.0029(13) -0.0007(13)
C2 0.0553(18) 0.0502(16) 0.0439(15) -0.0034(13) 0.0031(13) 0.0007(13)
C3 0.0589(19) 0.0525(17) 0.0489(16) -0.0068(13) 0.0046(14) -0.0002(14)
C4 0.0548(19) 0.0606(19) 0.0437(15) -0.0010(14) 0.0062(13) 0.0052(14)
C5 0.059(2) 0.077(2) 0.0491(17) -0.0002(16) 0.0020(15) 0.0028(16)
C6 0.061(2) 0.096(3) 0.0449(17) 0.0078(18) 0.0013(15) 0.0132(19)
O7 0.0868(17) 0.0800(17) 0.0618(14) 0.0215(12) 0.0085(12) 0.0237(14)
C7 0.068(2) 0.077(2) 0.0473(17) 0.0163(16) 0.0139(16) 0.0209(18)
C8 0.064(2) 0.0609(19) 0.0497(17) 0.0064(14) 0.0120(15) 0.0116(15)
C9 0.0551(18) 0.0594(18) 0.0413(15) 0.0037(13) 0.0086(13) 0.0092(14)
O10 0.0811(17) 0.0462(12) 0.0744(15) -0.0045(11) -0.0138(12) 0.0061(11)
C10 0.065(2) 0.0510(17) 0.0462(16) -0.0022(14) 0.0057(14) 0.0083(15)
C11 0.0569(19) 0.0474(16) 0.0442(15) -0.0031(13) 0.0044(13) 0.0048(13)
C12 0.0570(18) 0.0431(15) 0.0449(15) -0.0014(12) 0.0066(13) 0.0023(13)
C13 0.0546(18) 0.0461(15) 0.0404(14) -0.0048(12) 0.0072(12) 0.0017(13)
C14 0.0630(19) 0.0409(15) 0.0467(16) -0.0039(12) 0.0084(14) 0.0029(13)
O15 0.0878(16) 0.0458(12) 0.0551(12) -0.0079(10) -0.0026(11) -0.0072(11)
C15 0.069(2) 0.0451(16) 0.0444(15) -0.0074(13) 0.0081(14) -0.0039(14)
C16 0.0582(19) 0.0566(18) 0.0416(15) -0.0052(13) 0.0018(13) -0.0052(14)
C17 0.0545(18) 0.0457(15) 0.0436(15) 0.0011(12) 0.0045(13) 0.0022(13)
C18 0.0555(18) 0.0439(15) 0.0385(14) -0.0011(12) 0.0071(12) -0.0006(12)
C19 0.0564(18) 0.0418(15) 0.0383(14) -0.0018(11) 0.0070(12) 0.0011(12)
C20 0.0571(18) 0.0425(15) 0.0441(15) -0.0023(12) 0.0081(13) -0.0003(13)
C21 0.0518(17) 0.0445(15) 0.0431(15) 0.0017(12) 0.0037(12) -0.0021(12)
C22 0.070(2) 0.0458(16) 0.0420(15) -0.0023(13) 0.0048(13) -0.0029(14)
C23 0.075(2) 0.0475(17) 0.0410(15) 0.0058(13) 0.0016(14) -0.0066(14)
C24 0.063(2) 0.0420(15) 0.0504(17) 0.0060(13) 0.0016(14) -0.0022(13)
O25 0.0852(16) 0.0424(11) 0.0561(12) 0.0085(9) 0.0005(11) 0.0039(10)
C25 0.0610(19) 0.0434(16) 0.0473(16) -0.0013(12) 0.0068(13) 0.0000(13)
C26 0.0608(19) 0.0485(16) 0.0411(15) 0.0025(12) 0.0036(13) 0.0001(13)
C31 0.0526(18) 0.0412(15) 0.0461(15) -0.0010(12) -0.0007(13) 0.0013(12)
C32 0.0612(19) 0.0395(15) 0.0470(16) -0.0008(12) -0.0038(13) -0.0003(13)
C33 0.0581(19) 0.0488(16) 0.0473(16) 0.0028(13) 0.0034(13) -0.0009(13)
O34 0.0761(15) 0.0613(13) 0.0585(13) -0.0146(10) 0.0118(11) -0.0004(11)
C34 0.061(2) 0.0513(17) 0.0483(16) -0.0060(13) 0.0050(14) 0.0059(14)
C35 0.068(2) 0.0573(19) 0.064(2) -0.0196(16) 0.0072(16) -0.0077(16)
C36 0.062(2) 0.0586(19) 0.065(2) -0.0140(16) 0.0128(16) -0.0106(15)
C41 0.061(2) 0.0485(16) 0.0476(16) -0.0079(13) 0.0031(14) -0.0033(14)
C42 0.061(2) 0.0553(19) 0.071(2) 0.0007(16) 0.0050(16) -0.0037(15)
C43 0.078(3) 0.060(2) 0.080(2) 0.0129(18) 0.005(2) -0.0073(18)
O44 0.088(2) 0.108(2) 0.119(2) 0.0315(18) 0.0266(18) -0.0195(16)
C44 0.078(3) 0.077(2) 0.069(2) 0.0101(19) 0.0104(19) -0.017(2)
C45 0.072(2) 0.080(2) 0.068(2) -0.0031(19) 0.0178(18) -0.0061(19)
C46 0.073(2) 0.0569(19) 0.0588(19) -0.0057(15) 0.0089(16) -0.0004(16)
C51 0.090(3) 0.079(3) 0.125(4) 0.047(3) 0.028(3) 0.019(2)
C52 0.116(3) 0.0411(17) 0.065(2) -0.0074(15) 0.000(2) -0.0076(18)
C53 0.096(3) 0.0455(17) 0.068(2) 0.0040(16) 0.0042(19) 0.0088(17)
C54 0.080(2) 0.068(2) 0.067(2) -0.0253(17) 0.0073(18) -0.0007(18)
C55 0.104(4) 0.129(4) 0.101(3) 0.016(3) 0.032(3) -0.024(3)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C41 1.538(4) . ?
C1 C31 1.538(4) . ?
C1 C20 1.549(4) . ?
C1 C2 1.568(4) . ?
C2 C3 1.351(4) . ?
C2 C11 1.450(4) . ?
C3 C4 1.465(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.402(4) . ?
C4 C9 1.411(4) . ?
C5 C6 1.382(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.395(5) . ?
C6 H6 0.9500 . ?
O7 C7 1.383(4) . ?
O7 C51 1.441(5) . ?
C7 C8 1.374(4) . ?
C8 C9 1.404(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.478(4) . ?
O10 C10 1.239(3) . ?
C10 C11 1.477(4) . ?
C11 C12 1.367(4) . ?
C12 C13 1.457(4) . ?
C12 C20 1.458(4) . ?
C13 C14 1.393(4) . ?
C13 C18 1.413(4) . ?
C14 C15 1.399(4) . ?
C14 H14 0.9500 . ?
O15 C15 1.384(3) . ?
O15 C52 1.431(4) . ?
C15 C16 1.393(4) . ?
C16 C17 1.398(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.386(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.497(4) . ?
C19 C20 1.367(4) . ?
C19 C21 1.480(4) . ?
C21 C26 1.399(4) . ?
C21 C22 1.407(4) . ?
C22 C23 1.375(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.389(4) . ?
C23 H23 0.9500 . ?
C24 O25 1.375(3) . ?
C24 C25 1.396(4) . ?
O25 C53 1.421(4) . ?
C25 C26 1.391(4) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C31 C36 1.390(4) . ?
C31 C32 1.392(4) . ?
C32 C33 1.388(4) . ?
C32 H32 0.9500 . ?
C33 C34 1.391(4) . ?
C33 H33 0.9500 . ?
O34 C34 1.384(3) . ?
O34 C54 1.428(4) . ?
C34 C35 1.374(4) . ?
C35 C36 1.398(4) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C41 C46 1.377(4) . ?
C41 C42 1.403(4) . ?
C42 C43 1.383(5) . ?
C42 H42 0.9500 . ?
C43 C44 1.381(5) . ?
C43 H43 0.9500 . ?
O44 C44 1.385(4) . ?
O44 C55 1.403(5) . ?
C44 C45 1.382(5) . ?
C45 C46 1.402(5) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
C52 H52A 0.9800 . ?
C52 H52B 0.9800 . ?
C52 H52C 0.9800 . ?
C53 H53A 0.9800 . ?
C53 H53B 0.9800 . ?
C53 H53C 0.9800 . ?
C54 H54A 0.9800 . ?
C54 H54B 0.9800 . ?
C54 H54C 0.9800 . ?
C55 H55A 0.9800 . ?
C55 H55B 0.9800 . ?
C55 H55C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C41 C1 C31 114.1(2) . . ?
C41 C1 C20 109.9(2) . . ?
C31 C1 C20 113.5(2) . . ?
C41 C1 C2 112.4(2) . . ?
C31 C1 C2 106.4(2) . . ?
C20 C1 C2 99.7(2) . . ?
C3 C2 C11 121.4(3) . . ?
C3 C2 C1 128.7(3) . . ?
C11 C2 C1 109.9(2) . . ?
C2 C3 C4 120.1(3) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C9 117.1(3) . . ?
C5 C4 C3 121.9(3) . . ?
C9 C4 C3 120.9(3) . . ?
C6 C5 C4 121.7(3) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C7 120.0(3) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C7 O7 C51 116.3(3) . . ?
C8 C7 O7 123.9(3) . . ?
C8 C7 C6 120.2(3) . . ?
O7 C7 C6 115.9(3) . . ?
C7 C8 C9 119.8(3) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C8 C9 C4 121.2(3) . . ?
C8 C9 C10 118.2(3) . . ?
C4 C9 C10 120.7(3) . . ?
O10 C10 C11 121.4(3) . . ?
O10 C10 C9 122.9(3) . . ?
C11 C10 C9 115.7(3) . . ?
C12 C11 C2 109.9(2) . . ?
C12 C11 C10 129.0(3) . . ?
C2 C11 C10 121.1(3) . . ?
C11 C12 C13 140.9(3) . . ?
C11 C12 C20 110.9(2) . . ?
C13 C12 C20 108.1(2) . . ?
C14 C13 C18 122.3(3) . . ?
C14 C13 C12 131.7(3) . . ?
C18 C13 C12 106.0(2) . . ?
C13 C14 C15 117.5(3) . . ?
C13 C14 H14 121.3 . . ?
C15 C14 H14 121.3 . . ?
C15 O15 C52 117.0(2) . . ?
O15 C15 C16 116.0(3) . . ?
O15 C15 C14 123.0(3) . . ?
C16 C15 C14 121.0(3) . . ?
C15 C16 C17 120.6(3) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C18 C17 C16 119.7(3) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C17 C18 C13 118.9(2) . . ?
C17 C18 C19 131.7(3) . . ?
C13 C18 C19 109.3(2) . . ?
C20 C19 C21 131.1(2) . . ?
C20 C19 C18 106.9(2) . . ?
C21 C19 C18 122.0(2) . . ?
C19 C20 C12 109.7(2) . . ?
C19 C20 C1 140.8(2) . . ?
C12 C20 C1 109.5(2) . . ?
C26 C21 C22 116.8(2) . . ?
C26 C21 C19 122.8(2) . . ?
C22 C21 C19 120.4(2) . . ?
C23 C22 C21 121.9(3) . . ?
C23 C22 H22 119.0 . . ?
C21 C22 H22 119.0 . . ?
C22 C23 C24 120.2(3) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
O25 C24 C23 115.2(2) . . ?
O25 C24 C25 125.3(3) . . ?
C23 C24 C25 119.6(3) . . ?
C24 O25 C53 118.3(2) . . ?
C26 C25 C24 119.5(3) . . ?
C26 C25 H25 120.2 . . ?
C24 C25 H25 120.2 . . ?
C25 C26 C21 121.9(3) . . ?
C25 C26 H26 119.0 . . ?
C21 C26 H26 119.0 . . ?
C36 C31 C32 117.4(3) . . ?
C36 C31 C1 121.7(3) . . ?
C32 C31 C1 120.5(2) . . ?
C33 C32 C31 121.6(3) . . ?
C33 C32 H32 119.2 . . ?
C31 C32 H32 119.2 . . ?
C32 C33 C34 119.9(3) . . ?
C32 C33 H33 120.0 . . ?
C34 C33 H33 120.0 . . ?
C34 O34 C54 116.5(2) . . ?
C35 C34 O34 124.8(3) . . ?
C35 C34 C33 119.6(3) . . ?
O34 C34 C33 115.6(3) . . ?
C34 C35 C36 119.9(3) . . ?
C34 C35 H35 120.0 . . ?
C36 C35 H35 120.0 . . ?
C31 C36 C35 121.5(3) . . ?
C31 C36 H36 119.2 . . ?
C35 C36 H36 119.2 . . ?
C46 C41 C42 116.8(3) . . ?
C46 C41 C1 122.9(3) . . ?
C42 C41 C1 120.1(3) . . ?
C43 C42 C41 121.6(3) . . ?
C43 C42 H42 119.2 . . ?
C41 C42 H42 119.2 . . ?
C44 C43 C42 120.5(3) . . ?
C44 C43 H43 119.8 . . ?
C42 C43 H43 119.8 . . ?
C44 O44 C55 117.7(3) . . ?
C43 C44 C45 119.3(3) . . ?
C43 C44 O44 115.2(3) . . ?
C45 C44 O44 125.5(4) . . ?
C44 C45 C46 119.5(3) . . ?
C44 C45 H45 120.2 . . ?
C46 C45 H45 120.2 . . ?
C41 C46 C45 122.2(3) . . ?
C41 C46 H46 118.9 . . ?
C45 C46 H46 118.9 . . ?
O7 C51 H51A 109.5 . . ?
O7 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
O7 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
O15 C52 H52A 109.5 . . ?
O15 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
O15 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
O25 C53 H53A 109.5 . . ?
O25 C53 H53B 109.5 . . ?
H53A C53 H53B 109.5 . . ?
O25 C53 H53C 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
O34 C54 H54A 109.5 . . ?
O34 C54 H54B 109.5 . . ?
H54A C54 H54B 109.5 . . ?
O34 C54 H54C 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
O44 C55 H55A 109.5 . . ?
O44 C55 H55B 109.5 . . ?
H55A C55 H55B 109.5 . . ?
O44 C55 H55C 109.5 . . ?
H55A C55 H55C 109.5 . . ?
H55B C55 H55C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C41 C1 C2 C3 -63.9(4) . . . . ?
C31 C1 C2 C3 61.6(4) . . . . ?
C20 C1 C2 C3 179.7(3) . . . . ?
C41 C1 C2 C11 116.8(3) . . . . ?
C31 C1 C2 C11 -117.7(2) . . . . ?
C20 C1 C2 C11 0.5(3) . . . . ?
C11 C2 C3 C4 -1.1(4) . . . . ?
C1 C2 C3 C4 179.7(3) . . . . ?
C2 C3 C4 C5 -177.1(3) . . . . ?
C2 C3 C4 C9 2.2(4) . . . . ?
C9 C4 C5 C6 0.8(4) . . . . ?
C3 C4 C5 C6 -179.9(3) . . . . ?
C4 C5 C6 C7 0.3(5) . . . . ?
C51 O7 C7 C8 4.8(4) . . . . ?
C51 O7 C7 C6 -175.2(3) . . . . ?
C5 C6 C7 C8 -1.0(5) . . . . ?
C5 C6 C7 O7 179.0(3) . . . . ?
O7 C7 C8 C9 -179.6(3) . . . . ?
C6 C7 C8 C9 0.4(4) . . . . ?
C7 C8 C9 C4 0.8(4) . . . . ?
C7 C8 C9 C10 -179.6(3) . . . . ?
C5 C4 C9 C8 -1.4(4) . . . . ?
C3 C4 C9 C8 179.3(3) . . . . ?
C5 C4 C9 C10 179.1(3) . . . . ?
C3 C4 C9 C10 -0.2(4) . . . . ?
C8 C9 C10 O10 -3.4(4) . . . . ?
C4 C9 C10 O10 176.1(3) . . . . ?
C8 C9 C10 C11 177.9(3) . . . . ?
C4 C9 C10 C11 -2.6(4) . . . . ?
C3 C2 C11 C12 178.9(3) . . . . ?
C1 C2 C11 C12 -1.8(3) . . . . ?
C3 C2 C11 C10 -2.0(4) . . . . ?
C1 C2 C11 C10 177.4(2) . . . . ?
O10 C10 C11 C12 3.9(5) . . . . ?
C9 C10 C11 C12 -177.3(3) . . . . ?
O10 C10 C11 C2 -175.0(3) . . . . ?
C9 C10 C11 C2 3.7(4) . . . . ?
C2 C11 C12 C13 -177.6(3) . . . . ?
C10 C11 C12 C13 3.3(6) . . . . ?
C2 C11 C12 C20 2.4(3) . . . . ?
C10 C11 C12 C20 -176.7(3) . . . . ?
C11 C12 C13 C14 -3.2(6) . . . . ?
C20 C12 C13 C14 176.8(3) . . . . ?
C11 C12 C13 C18 179.6(4) . . . . ?
C20 C12 C13 C18 -0.4(3) . . . . ?
C18 C13 C14 C15 1.1(4) . . . . ?
C12 C13 C14 C15 -175.7(3) . . . . ?
C52 O15 C15 C16 177.3(3) . . . . ?
C52 O15 C15 C14 -2.5(4) . . . . ?
C13 C14 C15 O15 177.9(3) . . . . ?
C13 C14 C15 C16 -1.9(4) . . . . ?
O15 C15 C16 C17 -178.4(3) . . . . ?
C14 C15 C16 C17 1.5(4) . . . . ?
C15 C16 C17 C18 -0.1(4) . . . . ?
C16 C17 C18 C13 -0.7(4) . . . . ?
C16 C17 C18 C19 175.6(3) . . . . ?
C14 C13 C18 C17 0.2(4) . . . . ?
C12 C13 C18 C17 177.7(2) . . . . ?
C14 C13 C18 C19 -176.9(2) . . . . ?
C12 C13 C18 C19 0.6(3) . . . . ?
C17 C18 C19 C20 -177.2(3) . . . . ?
C13 C18 C19 C20 -0.6(3) . . . . ?
C17 C18 C19 C21 2.1(4) . . . . ?
C13 C18 C19 C21 178.7(2) . . . . ?
C21 C19 C20 C12 -178.9(3) . . . . ?
C18 C19 C20 C12 0.4(3) . . . . ?
C21 C19 C20 C1 4.2(6) . . . . ?
C18 C19 C20 C1 -176.5(3) . . . . ?
C11 C12 C20 C19 180.0(2) . . . . ?
C13 C12 C20 C19 0.0(3) . . . . ?
C11 C12 C20 C1 -2.1(3) . . . . ?
C13 C12 C20 C1 177.9(2) . . . . ?
C41 C1 C20 C19 59.6(5) . . . . ?
C31 C1 C20 C19 -69.5(4) . . . . ?
C2 C1 C20 C19 177.8(3) . . . . ?
C41 C1 C20 C12 -117.3(3) . . . . ?
C31 C1 C20 C12 113.6(3) . . . . ?
C2 C1 C20 C12 0.9(3) . . . . ?
C20 C19 C21 C26 45.7(5) . . . . ?
C18 C19 C21 C26 -133.5(3) . . . . ?
C20 C19 C21 C22 -135.4(3) . . . . ?
C18 C19 C21 C22 45.4(4) . . . . ?
C26 C21 C22 C23 -2.1(4) . . . . ?
C19 C21 C22 C23 178.9(3) . . . . ?
C21 C22 C23 C24 1.1(5) . . . . ?
C22 C23 C24 O25 -178.9(3) . . . . ?
C22 C23 C24 C25 0.4(5) . . . . ?
C23 C24 O25 C53 -177.4(3) . . . . ?
C25 C24 O25 C53 3.4(4) . . . . ?
O25 C24 C25 C26 178.3(3) . . . . ?
C23 C24 C25 C26 -0.9(4) . . . . ?
C24 C25 C26 C21 -0.2(4) . . . . ?
C22 C21 C26 C25 1.6(4) . . . . ?
C19 C21 C26 C25 -179.4(3) . . . . ?
C41 C1 C31 C36 27.5(4) . . . . ?
C20 C1 C31 C36 154.5(3) . . . . ?
C2 C1 C31 C36 -97.0(3) . . . . ?
C41 C1 C31 C32 -159.8(3) . . . . ?
C20 C1 C31 C32 -32.8(4) . . . . ?
C2 C1 C31 C32 75.7(3) . . . . ?
C36 C31 C32 C33 0.5(4) . . . . ?
C1 C31 C32 C33 -172.5(2) . . . . ?
C31 C32 C33 C34 -0.7(4) . . . . ?
C54 O34 C34 C35 5.1(4) . . . . ?
C54 O34 C34 C33 -175.1(3) . . . . ?
C32 C33 C34 C35 -0.1(4) . . . . ?
C32 C33 C34 O34 -180.0(3) . . . . ?
O34 C34 C35 C36 -179.2(3) . . . . ?
C33 C34 C35 C36 1.0(5) . . . . ?
C32 C31 C36 C35 0.3(5) . . . . ?
C1 C31 C36 C35 173.3(3) . . . . ?
C34 C35 C36 C31 -1.1(5) . . . . ?
C31 C1 C41 C46 -135.3(3) . . . . ?
C20 C1 C41 C46 96.0(3) . . . . ?
C2 C1 C41 C46 -14.1(4) . . . . ?
C31 C1 C41 C42 49.0(4) . . . . ?
C20 C1 C41 C42 -79.7(3) . . . . ?
C2 C1 C41 C42 170.2(3) . . . . ?
C46 C41 C42 C43 1.7(5) . . . . ?
C1 C41 C42 C43 177.7(3) . . . . ?
C41 C42 C43 C44 -0.2(5) . . . . ?
C42 C43 C44 C45 -1.2(6) . . . . ?
C42 C43 C44 O44 178.2(3) . . . . ?
C55 O44 C44 C43 -165.6(4) . . . . ?
C55 O44 C44 C45 13.7(6) . . . . ?
C43 C44 C45 C46 0.9(5) . . . . ?
O44 C44 C45 C46 -178.4(3) . . . . ?
C42 C41 C46 C45 -2.0(5) . . . . ?
C1 C41 C46 C45 -177.8(3) . . . . ?
C44 C45 C46 C41 0.7(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        27.45
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.050